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Because Cuba and the United States have had a strained political relationship since the 1960s, there had been no direct transport route from Cuba to Florida despite the short distance for many years. As of 2014, there are direct flights from the United States to Cuba for certain individuals, primarily those individuals with relatives living in Cuba. Over the years, many Cuban immigrants settled in South Florida, adding Cuban influence to the area.

In 2013, Diana Nyad, a 64-year-old American, was the second long-distance swimmer to complete the swim from Havana to Key West.